CA2677995A1 - Derive d'acylguanidine - Google Patents
Derive d'acylguanidine Download PDFInfo
- Publication number
- CA2677995A1 CA2677995A1 CA002677995A CA2677995A CA2677995A1 CA 2677995 A1 CA2677995 A1 CA 2677995A1 CA 002677995 A CA002677995 A CA 002677995A CA 2677995 A CA2677995 A CA 2677995A CA 2677995 A1 CA2677995 A1 CA 2677995A1
- Authority
- CA
- Canada
- Prior art keywords
- fab
- lower alkyl
- carbazole
- group
- carboxamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 210
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 47
- 206010012289 Dementia Diseases 0.000 claims abstract description 37
- 108010006590 serotonin 5 receptor Proteins 0.000 claims abstract description 35
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 16
- 208000020925 Bipolar disease Diseases 0.000 claims abstract description 16
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims abstract description 15
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 80
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- -1 isoxazolylmethyl Chemical group 0.000 claims description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 23
- 239000004480 active ingredient Substances 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 18
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000005936 piperidyl group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 11
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 229940075993 receptor modulator Drugs 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 4
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- CUFTYTRCDRZTNK-UHFFFAOYSA-N 5-chloro-n-(diaminomethylidene)-9-propan-2-ylcarbazole-2-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C=C2N(C(C)C)C3=CC=CC(Cl)=C3C2=C1 CUFTYTRCDRZTNK-UHFFFAOYSA-N 0.000 claims description 2
- CEUVHVHNKRQUJB-UHFFFAOYSA-N 9-benzyl-n-(diaminomethylidene)carbazole-2-carboxamide Chemical compound C=1C(C(=O)N=C(N)N)=CC=C(C2=CC=CC=C22)C=1N2CC1=CC=CC=C1 CEUVHVHNKRQUJB-UHFFFAOYSA-N 0.000 claims description 2
- YVRNXHHORCXTST-UHFFFAOYSA-N 9-cyclobutyl-n-(diaminomethylidene)carbazole-2-carboxamide Chemical compound C=1C(C(=O)N=C(N)N)=CC=C(C2=CC=CC=C22)C=1N2C1CCC1 YVRNXHHORCXTST-UHFFFAOYSA-N 0.000 claims description 2
- BJBWUUOXLRSMGD-UHFFFAOYSA-N 9-cyclohexyl-n-(diaminomethylidene)carbazole-2-carboxamide Chemical compound C=1C(C(=O)N=C(N)N)=CC=C(C2=CC=CC=C22)C=1N2C1CCCCC1 BJBWUUOXLRSMGD-UHFFFAOYSA-N 0.000 claims description 2
- MCQPFEIRPOCVIL-UHFFFAOYSA-N n-(diaminomethylidene)-4,5-difluoro-9-(oxan-4-yl)carbazole-2-carboxamide Chemical compound C=1C(C(=O)N=C(N)N)=CC(F)=C(C2=C(F)C=CC=C22)C=1N2C1CCOCC1 MCQPFEIRPOCVIL-UHFFFAOYSA-N 0.000 claims description 2
- OVLHPLBZHQTZKT-UHFFFAOYSA-N n-(diaminomethylidene)-4-methyl-9-(oxan-4-yl)carbazole-2-carboxamide Chemical compound C12=CC=CC=C2C=2C(C)=CC(C(=O)N=C(N)N)=CC=2N1C1CCOCC1 OVLHPLBZHQTZKT-UHFFFAOYSA-N 0.000 claims description 2
- FSWFPGLILYYPDO-UHFFFAOYSA-N n-(diaminomethylidene)-5-fluoro-4-methyl-9-(oxan-4-yl)carbazole-2-carboxamide Chemical compound C12=CC=CC(F)=C2C=2C(C)=CC(C(=O)N=C(N)N)=CC=2N1C1CCOCC1 FSWFPGLILYYPDO-UHFFFAOYSA-N 0.000 claims description 2
- UYCHZINZPKVOSA-UHFFFAOYSA-N n-(diaminomethylidene)-9-(4,4-difluorocyclohexyl)carbazole-2-carboxamide Chemical compound C=1C(C(=O)N=C(N)N)=CC=C(C2=CC=CC=C22)C=1N2C1CCC(F)(F)CC1 UYCHZINZPKVOSA-UHFFFAOYSA-N 0.000 claims description 2
- TYTXZGAGGWEAGT-UHFFFAOYSA-N n-(diaminomethylidene)-9-(4-fluorocyclohex-3-en-1-yl)-5-methylcarbazole-2-carboxamide Chemical compound C12=CC(C(=O)N=C(N)N)=CC=C2C=2C(C)=CC=CC=2N1C1CCC(F)=CC1 TYTXZGAGGWEAGT-UHFFFAOYSA-N 0.000 claims description 2
- KLORIOHBIMIFCM-UHFFFAOYSA-N n-(diaminomethylidene)-9-piperidin-4-ylcarbazole-2-carboxamide Chemical compound C=1C(C(=O)N=C(N)N)=CC=C(C2=CC=CC=C22)C=1N2C1CCNCC1 KLORIOHBIMIFCM-UHFFFAOYSA-N 0.000 claims description 2
- RHTBRDZMAOUHSQ-UHFFFAOYSA-N n-(n'-methylcarbamimidoyl)-9-(oxan-4-yl)carbazole-2-carboxamide Chemical compound C=1C(C(=O)N=C(N)NC)=CC=C(C2=CC=CC=C22)C=1N2C1CCOCC1 RHTBRDZMAOUHSQ-UHFFFAOYSA-N 0.000 claims description 2
- IKRMVDWHSLUFHJ-UHFFFAOYSA-N n-[n'-(3-methoxypropyl)carbamimidoyl]-9-(oxan-4-yl)carbazole-2-carboxamide Chemical compound C=1C(C(=O)N=C(N)NCCCOC)=CC=C(C2=CC=CC=C22)C=1N2C1CCOCC1 IKRMVDWHSLUFHJ-UHFFFAOYSA-N 0.000 claims description 2
- IHMKTLBGHRJQNK-UHFFFAOYSA-N n-[n'-[(2,6-dimethoxyphenyl)methyl]carbamimidoyl]-9-(oxan-4-yl)carbazole-2-carboxamide Chemical compound COC1=CC=CC(OC)=C1CNC(N)=NC(=O)C1=CC=C2C3=CC=CC=C3N(C3CCOCC3)C2=C1 IHMKTLBGHRJQNK-UHFFFAOYSA-N 0.000 claims description 2
- JIWOJOQWUMXPAB-UHFFFAOYSA-N n-[n'-[(4-methoxyphenyl)methyl]carbamimidoyl]-9-(oxan-4-yl)carbazole-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(N)=NC(=O)C1=CC=C2C3=CC=CC=C3N(C3CCOCC3)C2=C1 JIWOJOQWUMXPAB-UHFFFAOYSA-N 0.000 claims description 2
- XNMHKLHSOLIREN-UHFFFAOYSA-N n-(diaminomethylidene)-5-(hydroxymethyl)-9-propan-2-ylcarbazole-2-carboxamide Chemical compound C1=C(C(=O)N=C(N)N)C=C2N(C(C)C)C3=CC=CC(CO)=C3C2=C1 XNMHKLHSOLIREN-UHFFFAOYSA-N 0.000 claims 1
- WSRHXDDOXXRLQI-UHFFFAOYSA-N n-(diaminomethylidene)-5-fluoro-9-(oxan-4-yl)carbazole-2-carboxamide Chemical compound C=1C(C(=O)N=C(N)N)=CC=C(C2=C(F)C=CC=C22)C=1N2C1CCOCC1 WSRHXDDOXXRLQI-UHFFFAOYSA-N 0.000 claims 1
- INLHKXYBOMSRBS-UHFFFAOYSA-N n-(diaminomethylidene)-9-(thiophen-2-ylmethyl)carbazole-2-carboxamide Chemical compound C=1C(C(=O)N=C(N)N)=CC=C(C2=CC=CC=C22)C=1N2CC1=CC=CS1 INLHKXYBOMSRBS-UHFFFAOYSA-N 0.000 claims 1
- WYNLMRRPMIHWFO-UHFFFAOYSA-N n-[n'-(cyclopropylmethyl)carbamimidoyl]-9-(oxan-4-yl)carbazole-2-carboxamide Chemical compound C=1C=C(C2=CC=CC=C2N2C3CCOCC3)C2=CC=1C(=O)N=C(N)NCC1CC1 WYNLMRRPMIHWFO-UHFFFAOYSA-N 0.000 claims 1
- NORVLGNLRAQZRS-UHFFFAOYSA-N n-[n'-[(3-methoxyphenyl)methyl]carbamimidoyl]-9-(oxan-4-yl)carbazole-2-carboxamide Chemical compound COC1=CC=CC(CNC(N)=NC(=O)C=2C=C3C(C4=CC=CC=C4N3C3CCOCC3)=CC=2)=C1 NORVLGNLRAQZRS-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 18
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract description 16
- 208000028698 Cognitive impairment Diseases 0.000 abstract description 12
- 208000010877 cognitive disease Diseases 0.000 abstract description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 6
- 125000005842 heteroatom Chemical group 0.000 abstract description 6
- 230000000144 pharmacologic effect Effects 0.000 abstract description 5
- 125000000168 pyrrolyl group Chemical group 0.000 abstract description 5
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 230000000069 prophylactic effect Effects 0.000 abstract 2
- 230000001225 therapeutic effect Effects 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 154
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 142
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 142
- 229910052739 hydrogen Inorganic materials 0.000 description 113
- 238000004519 manufacturing process Methods 0.000 description 74
- 238000006243 chemical reaction Methods 0.000 description 71
- 238000005481 NMR spectroscopy Methods 0.000 description 66
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 229910003827 NRaRb Inorganic materials 0.000 description 27
- 238000010438 heat treatment Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- 241001465754 Metazoa Species 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000007858 starting material Substances 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000003795 chemical substances by application Substances 0.000 description 18
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- 238000002360 preparation method Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- 208000024891 symptom Diseases 0.000 description 15
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Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- Pain & Pain Management (AREA)
- Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007028089 | 2007-02-07 | ||
JP2007-028089 | 2007-02-07 | ||
PCT/JP2008/051962 WO2008096791A1 (fr) | 2007-02-07 | 2008-02-06 | Dérivé d'acylguanidine |
Publications (1)
Publication Number | Publication Date |
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CA2677995A1 true CA2677995A1 (fr) | 2008-08-14 |
Family
ID=39681697
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002677995A Abandoned CA2677995A1 (fr) | 2007-02-07 | 2008-02-06 | Derive d'acylguanidine |
Country Status (8)
Country | Link |
---|---|
US (1) | US20100324017A1 (fr) |
EP (1) | EP2119704A4 (fr) |
JP (1) | JP5287257B2 (fr) |
KR (1) | KR20090114439A (fr) |
CN (1) | CN101627013A (fr) |
CA (1) | CA2677995A1 (fr) |
MX (1) | MX2009008507A (fr) |
WO (1) | WO2008096791A1 (fr) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110207729A1 (en) | 2007-08-10 | 2011-08-25 | Astellas Pharma Inc. | Bicyclic acylguanidine derivative |
CN104387382A (zh) | 2008-03-24 | 2015-03-04 | 梅迪维新技术公司 | 吡啶并[3,4-b]吲哚和应用方法 |
TW201116281A (en) | 2009-08-06 | 2011-05-16 | Astellas Pharma Inc | N atom containing ring acylguanidine derivatives |
JP5791611B2 (ja) * | 2009-09-23 | 2015-10-07 | メディベイション テクノロジーズ, インコーポレイテッド | ピリド[3,4−b]インドールおよび使用方法 |
US20120039804A1 (en) * | 2010-06-04 | 2012-02-16 | Philippe Diaz | Novel Tricyclic Modulators of Cannabinoid Receptors |
KR20140003484A (ko) * | 2011-02-02 | 2014-01-09 | 아스테라스 세이야쿠 가부시키가이샤 | 테트라히드로이소퀴놀린 유도체 |
CN104326937B (zh) | 2014-09-03 | 2016-08-24 | 天津市肿瘤研究所 | 抗肿瘤化合物及其医药用途 |
CN110753683B (zh) * | 2017-04-11 | 2024-02-09 | 吉斯诺治疗公司 | 咔唑化合物及其使用方法 |
WO2021193708A1 (fr) * | 2020-03-25 | 2021-09-30 | Jnc株式会社 | Composé, composition de cristaux liquides et élément d'affichage à cristaux liquides |
CN112375029B (zh) * | 2020-11-11 | 2022-03-18 | 湖北省生物农药工程研究中心 | 一种咔唑生物碱衍生物及其制备方法和用途 |
US20240244954A1 (en) * | 2021-09-29 | 2024-07-18 | Beijing Boe Technology Development Co., Ltd. | Quantum dot ligand, quantum dot-ligand system and quantum dot material |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
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US41696A (en) | 1864-02-23 | Improvement in railroad-track raisers | ||
US5082871A (en) | 1986-12-22 | 1992-01-21 | General Electric Company | UV-activation of addition cure silicon coatings |
US6221884B1 (en) * | 1997-06-04 | 2001-04-24 | Eli Lilly And Company | Carboxamides useful as 5-HT1F agonists |
ID23053A (id) * | 1997-06-04 | 2000-01-20 | Lilly Co Eli | Karboksamida yang digunakan sebagai agonis 5-ht <if> |
DE19724979A1 (de) | 1997-06-13 | 1998-12-17 | Basf Ag | 3-substituierte Pyrido [3,4,5]thieno[2,3-d]pyrimidin-Derivate, ihre Herstellung und Verwendung |
DK1032556T3 (da) * | 1997-10-21 | 2008-03-25 | Wyeth Corp | Farmaceutisk aktive forbindelser og anvendelsesfremgangsmåder |
FR2784678B1 (fr) * | 1998-09-23 | 2002-11-29 | Sod Conseils Rech Applic | Nouveaux derives de n-(iminomethyl)amines, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant |
GB0309781D0 (en) | 2003-04-29 | 2003-06-04 | Glaxo Group Ltd | Compounds |
RU2006107371A (ru) * | 2004-02-20 | 2006-09-10 | Астеллас Фарма Инк. (Jp) | Флуореновые производные |
US20080161419A1 (en) | 2004-02-20 | 2008-07-03 | Shinobu Akuzawa | Prophylactic Antimigraine Agents |
AU2006233867A1 (en) | 2005-04-11 | 2006-10-19 | F. Hoffmann-La Roche Ag | (3,4-dihydro-quinazolin-2-yl)-indan-1-yl-amines |
CA2617473A1 (fr) * | 2005-08-08 | 2007-02-15 | Astellas Pharma Inc. | Derive d'acylguanidine ou sel de celui-ci |
-
2008
- 2008-02-06 KR KR1020097018533A patent/KR20090114439A/ko not_active Application Discontinuation
- 2008-02-06 CA CA002677995A patent/CA2677995A1/fr not_active Abandoned
- 2008-02-06 MX MX2009008507A patent/MX2009008507A/es not_active Application Discontinuation
- 2008-02-06 US US12/526,250 patent/US20100324017A1/en not_active Abandoned
- 2008-02-06 JP JP2008557144A patent/JP5287257B2/ja not_active Expired - Fee Related
- 2008-02-06 CN CN200880004202A patent/CN101627013A/zh active Pending
- 2008-02-06 WO PCT/JP2008/051962 patent/WO2008096791A1/fr active Application Filing
- 2008-02-06 EP EP08710858A patent/EP2119704A4/fr not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
US20100324017A1 (en) | 2010-12-23 |
EP2119704A4 (fr) | 2011-06-15 |
CN101627013A (zh) | 2010-01-13 |
KR20090114439A (ko) | 2009-11-03 |
WO2008096791A1 (fr) | 2008-08-14 |
MX2009008507A (es) | 2009-08-20 |
EP2119704A1 (fr) | 2009-11-18 |
JPWO2008096791A1 (ja) | 2010-05-27 |
JP5287257B2 (ja) | 2013-09-11 |
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